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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.4K
Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
2.4K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.1K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.9K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
2.9K
Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

3.7K
Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
3.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.4K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.4K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

12.2K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Light-Activated Olefin Metathesis: Catalyst Development, Synthesis, and Applications.

Or Eivgi1, Ravindra S Phatake1, Noy B Nechmad1

  • 1Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel.

Accounts of Chemical Research
|September 29, 2020
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Summary

Researchers developed dormant ruthenium-based olefin metathesis catalysts activated by light. Ligand modifications and external stimuli enable precise control over reactions, leading to applications in 3D printing and stereolithography.

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Catalyst tuning is crucial for optimizing chemical reactions.
  • Ruthenium-based olefin metathesis is highly sensitive to ligand modifications.
  • Previous work demonstrated photoactive catalysts via sulfur-chelation.

Purpose of the Study:

  • To present a perspective on developing dormant olefin metathesis catalysts activated by external stimuli, particularly light.
  • To explore the systematic development of light-activated catalysts and chromatic-orthogonal synthetic schemes.
  • To summarize thermal activation experiments leading to photoactivation discoveries.

Main Methods:

  • Investigated the properties of cis-dichlororuthenium benzylidenes.
  • Explored disruption of ligand-to-metal bonds for activation.
  • Utilized specific light wavelengths to dissociate sulfur-ruthenium bonds.
  • Modified N-heterocyclic carbene (NHC) and cyclic alkyl amino carbene (CAAC) ligands.
  • Employed sulfoxides and phosphites to induce latency.

Main Results:

  • Discovered photoactivation in sulfur-chelated benzylidene catalysts.
  • Developed noncommutative catalytic chromatic-orthogonal processes.
  • Enabled combination of photochemistry with photoinduced olefin metathesis.
  • Achieved novel selectivities using light-absorbing molecules.
  • Enhanced light-induced activity and selectivity through ligand alterations.
  • Expanded the spectrum of light activators using electron-rich sulfoxides and phosphites.

Conclusions:

  • Light serves as an effective external stimulus for activating dormant olefin metathesis catalysts.
  • Ligand design is key to controlling catalyst activity, selectivity, and activation wavelengths.
  • Photoactivated catalysts offer potential in advanced applications like stereolithography and 3D printing.